Potassium Carbonate → HCID 178505083, compound

HRID 1641312Notes

Reaction equation

HRID 1641312 reaction equation
[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH2:26])[CH:20]=4)[CH2:14][CH2:13]3)[N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:10](=[O:34])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=4)[CH2:25][NH:26][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:14][CH2:13]3)[N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:10](=[O:34])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 178509763HCID 178509763, compound

Product 1

HCID 178505083HCID 178505083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 mL CH2Cl2 suspension of 0.05 g (0.11 mmol) 4-(cyclohexylamino)-8-[3-(aminomethyl)benzyl]-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (Example (7-12)), 0.02 mL (0.22 mmol) methanesulfonyl chloride and excess K2CO3 was allowed to stir at rt overnight. The reaction was filtered and concentrated. The remaining oil was dissolved in 0.5 mL CH2Cl2 and purified on an Isco automated system affixed with a Biotage Flash 25(S) cartridge eluted at 20 mL/min with 0-5% MeOH in CH2Cl2 over 15 min and hold at 5% MeOH for 30 min. The product eluted second, pure by HPLC/MS and NMR. 1H NMR (400 MHz, CDCl3) δ 7.79-7.83 (m, 1H), 7.45-7.54 (m, 2H), 7.33-7.4 (m, 2H), 7.12-7.14 (m, 1H), 6.96-7.05 (m, 3H), 4.31-4.39 (m, 1H), 3.92-4.05 (m, 1H), 3.48-3.52 (m, 1H), 2.65-2.80 (m, 2H), 2.4-2.50 (m, 2H), 1.90-2.20 (m, 6H), 1.62-1.8 (m, 4H), 1.55 (s, 3H), 1.30-1.50 (m, 2H), 1.15-1.30 (m, 4H). MS 542.4

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutionThe remaining oil was dissolved in 0.5 mL CH2Cl2
  4. custompurified on an Isco automated system
  5. washeluted at 20 mL/min with 0-5% MeOH in CH2Cl2 over 15 min
  6. waithold at 5% MeOH for 30 min
  7. washThe product eluted second, pure by HPLC/MS and NMR

Sources & evidence

ORD record
ord-c5c5636fb86244648693e4cf303fe3df
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

Loading…